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Synthesis of novel 1,2,3-triazole-containing pyridine–pyrazole amide derivatives based on one-pot click reaction and their evaluation for potent nematicidal activity against Meloidogyne incognita

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Abstract

In order to find a novel, leading nematicide compound, a series of pyridine–pyrazole amide derivatives containing 1,2,3-triazoles were synthesized via click chemistry in a one-pot reaction. Their structures were characterized by proton nuclear magnetic resonance ( 1H NMR), 13C NMR, 19F NMR and high-resolution mass spectrometry (HRMS). Preliminary bioassays showed that most of the synthesized compounds exhibited good inhibitory activity in vivo against Meloidogyne incognita at 25 mg L−1. Among the tested compounds, 3a, 3e, 3f, 3g, 3j, 3m, 3q, 3s, 3t, 3v and 3w exhibited 100 % inhibition rates. Moreover, 3k displayed a 92.4 % inhibitory activity at 10 mg L−1. This investigation suggested that this pyridine–pyrazole amide containing a 1,2,3-triazole scaffold could be further optimized to explore novel, high-bioactivity nematicidal leads.

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Acknowledgments

This work was financially supported by the National High Technology Research and Development Program of China (863 Program, 2013AA065202). This work was also partly supported by National Natural Science Foundation of China (21272071) and the Fundamental Research Funds for the Central Universities.

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Authors and Affiliations

  1. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China

    Xiulei Chen, Youxin Xiao, Gaolei Wang, Zhong Li & Xiaoyong Xu

  2. Shanghai Collaborative Innovation Center for Biomanufacturing Technology, 130 Meilong Road, Shanghai, 200237, China

    Zhong Li & Xiaoyong Xu

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  1. Xiulei Chen
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  2. Youxin Xiao
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  3. Gaolei Wang
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  4. Zhong Li
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  5. Xiaoyong Xu
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Correspondence to Xiaoyong Xu.

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Chen, X., Xiao, Y., Wang, G. et al. Synthesis of novel 1,2,3-triazole-containing pyridine–pyrazole amide derivatives based on one-pot click reaction and their evaluation for potent nematicidal activity against Meloidogyne incognita . Res Chem Intermed 42, 5495–5508 (2016). https://doi.org/10.1007/s11164-015-2381-y

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  • DOI: https://doi.org/10.1007/s11164-015-2381-y

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